$109 Cheap flight deals from Chicago (CHI) to Islamorada (MIA)
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This Weekend's Flight Deals from Chicago to Islamorada
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
O'Hare Intl.
MIA
Miami Intl.
$284 Roundtrip, just found
$284
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$310 Roundtrip, just found
$310
Roundtrip
just found
RFD
Greater Rockford
MIA
Miami Intl.
$455 Roundtrip, found 4 days ago
$455
Roundtrip
found 4 days ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$516 Roundtrip, found 11 hours ago
$516
Roundtrip
found 11 hours ago
Airfares from $109 One Way, $209 Round Trip from Chicago to Islamorada
Prices starting at $209 for return flights and $109 for one-way flights to Islamorada were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
MIA
Miami
$209 Roundtrip, found 11 hours ago
$209
Roundtrip
found 11 hours ago
MDW
Chicago
MIA
Miami
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
ORD
Chicago
EYW
Key West
$339 Roundtrip, found 2 hours ago
$339
Roundtrip
found 2 hours ago
ORD
Chicago
EYW
Key West
$352 Roundtrip, found 2 days ago
$352
Roundtrip
found 2 days ago
MDW
Chicago
EYW
Key West
$359 Roundtrip, found 2 days ago
$359
Roundtrip
found 2 days ago
Islamorada economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Park Royal Miami Beach managed by Accor
8.8/10 Excellent! (191 reviews)
Oct 28 - Oct 31
3 night stay
Chicago (CHI) to Miami (MIA)
United • Roundtrip • Coach
Save 100% on your flight
Price was $784, price is now $455 per person
$455
per person
found 15 hours ago
Had been to Ft. Lauderdale and wanted to check for a decent none night stay in Miami and found this hotel Thro Expedia . Expedia rated this high and happy that we chose this place . Nice location. 5 mins off the beach . The beach is just walkable from this hotel. Very good service . The guy in lobby was very helpful . There was a donminos pizza next door , which was very useful for kids.
Amenities were decent . They had an outdoor swimming pool . Slightly smaller .. there were 2-3 families swimming and it was almost full :) washer dryer worked but it was good .. elevator was small and sometimes slow . We didn’t find a gym. No complimentary breakfast.. parking was a bit wierd and cramped ! They charged per night which was slightly expensive .
The rooms were awesome ! It was good sized for the price . Also had a kitchen.. though we didn’t use the kitchen , it is very good to have , just incase . Bed was comfortable .. bathrooms were neat . Price wise I think this room was very good and value for money . Wanted to give 3 , but just for the room and pricing , I’m giving it a 4 . Good experience overall .
Reviewed on Sep 1, 2026
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
Oct 15 - Oct 20
5 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • Coach
Price was $19,913, price is now $10,026 per person
$10,026
per person
found 16 hours ago
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
5.0-star property
EAST Miami Residences
9.2/10 Wonderful! (149 reviews)
Oct 23 - Oct 26
3 night stay
Chicago (CHI) to Miami (MIA)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,647, price is now $996 per person
$996
per person
found 17 hours ago
The room was really nice, there are small things that can be improved but overall nice.
Reviewed on Aug 25, 2026
Islamorada business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Renaissance Fort Lauderdale Marina Hotel
8.2/10 Very Good! (1,004 reviews)
Oct 23 - Oct 25
2 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Roundtrip • BusinessClass
Price was $799, price is now $697 per person
$697
per person
found 1 day ago
Cockroaches in the rooms
Reviewed on Sep 4, 2026
Islamorada first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hyatt Place Delray Beach
9.2/10 Wonderful! (510 reviews)
Oct 16 - Oct 22
6 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (CHI)
Delta • FirstClass
Price was $1,386, price is now $1,270 per person
$1,270
per person
found 1 day ago
The outdoor pool had only 3 umbrellas for the entire pool deck area, additionally there were no F & B amenities.
Reviewed on Sep 4, 2026
4.5-star property
The Seagate Hotel, Golf & Beach Club, Autograph Collection
9/10 Wonderful! (1,097 reviews)
Oct 16 - Oct 22
6 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (CHI)
Delta • FirstClass
Price was $1,826, price is now $1,817 per person
$1,817
per person
found 1 day ago
More About Flying To Islamorada from Chicago
Route Information for Flights from Chicago to Islamorada
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Islamorada
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.